Winsted, CT Homes

• 

  $290,000 Sold Aug 28, 2025

  • 1,978 Sq Ft
  • $147/SF
  • 49 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1880

  279 Pratt St, Winsted, CT 06098

  Perched atop Pratt Street in Winsted, this traditional farmhouse offers a peaceful retreat on a generous 1.75-acre lot. Tucked away from the hustle and bustle, the property provides a quiet sanctuary surrounded by nature, perfect for those yearning to live out their farming dreams. The home itself features a classic farmhouse charm with inviting living spaces. You'll find warm hardwood floors

  Michelle Grant Coldwell Banker Premier Real Estate

  279 Pratt St, Winsted, CT 06098
• 

  Est $284,322 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  174 Wallens St Unit C3, Winsted, CT 06098

  174 Wallens St Unit C3, Winsted, CT 06098
• 

  

  

  /33

  $380,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft

  166 Torringford St, Winsted, CT 06098

  Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home combines a tasteful modern style mixed with rustic charm. Inside the fully renovated home offers a sprawling kitchen with ample counter and cabinet space, a breakfast bar with elegant quartz countertops and newer stainless steel appliances. The space is open to the dining area

  Lana Van Valkenburgh Vision Real Estate

  166 Torringford St, Winsted, CT 06098
• 

  $388,000 Sold Aug 27, 2025

  • 2,403 Sq Ft
  • $161/SF
  • 70 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1868

  409 N Main St, Winsted, CT 06098

  This versatile 2-family home would make a perfect owner occupant first floor unit with 3 bedrooms; with a 2 bedroom second floor apartment. Private entrances with separate utilities. Let your rental income help pay your mortgage. Each unit comes with formal living and dining rooms. Pellet stove in the main dining room. Refinished wide pine flooring. Large main Kitchen with lots of cabinet space

  Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
• 

  Est $299,164 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  17 Colony Dr, Winsted, CT 06098

  17 Colony Dr, Winsted, CT 06098
• 

  

  /36

  $299,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  152 E Lake St, Winsted, CT 06098

  Well-maintained and move-in ready, this charming one-level ranch offers 900 square feet of comfortable living just steps from Highland Lake. Featuring 2 bedrooms and 2 full bathrooms, this home is perfect as a full-time residence, weekend retreat, or summer getaway. Enjoy lake living without the high taxes, with public water and sewer already in place. The property includes a private backyard

  Bryan Palladino Showcase Realty, Inc.

  152 E Lake St, Winsted, CT 06098
• 

  $172,500 Sold Aug 25, 2025

  • 1,446 Sq Ft
  • $119/SF
  • 43 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  415 N Main St, Winsted, CT 06098

  This charming 3-bedroom, 1-bath single-family home offers a great opportunity for homeowners or investors looking to build equity. Located close to downtown Winsted, this home features newer kitchen appliances, including a natural gas range, and a convenient main-level laundry area tucked inside a cozy pantry. A pellet stove in the dining room-currently not hooked up-adds potential for

  Jeffrey Liskin Northwest CT Realty

  415 N Main St, Winsted, CT 06098
• 

  Est $673,198 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,318 Sq Ft

  715 W Wakefield Blvd, Winsted, CT 06098

  715 W Wakefield Blvd, Winsted, CT 06098
• 

  

  /16

  $280,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 1.5 Baths
  • 1,323 Sq Ft

  331 Colebrook Rd, Winsted, CT 06098

  Nestled in the scenic Litchfield Hills, this charming 2-bedroom, 1.5-bath Cape has been lovingly restored over the past 11 years and thoughtfully updated with room to expand. Combining modern convenience with timeless character, improvements & remodeling include electrical upgrades, replacement of the majority of the windows in the house, insulation, newer appliances, a new back door, refinished

  Alison Malkin Essentia Realty

  331 Colebrook Rd, Winsted, CT 06098
• 

  $236,434 Sold Aug 25, 2025

  • 674 Sq Ft
  • $351/SF
  • 40 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1923

  343 W Wakefield Blvd, Winsted, CT 06098

  Your oasis awaits!!! Schedule your appointment today and come view this adorable Bungalow. There is so much potential to be made here. Bring your ideas and creativity as the seller is motivated, bring all offers!!!

  Patrick Precourt Dorrance Realty

  343 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $277,005 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  159 Pratt St, Winsted, CT 06098

  159 Pratt St, Winsted, CT 06098
• 

  

  /21

  $299,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft

  15 John St, Winsted, CT 06098

  Feels Like New - Without the New Construction Price! Looking for a move-in ready home that won't break the bank? This freshly renovated 3-bedroom, 2-bath home has been updated from top to bottom - with a brand-new roof, siding, doors (inside and out), electrical, plumbing, carpet, kitchen, and two full bathrooms. Everything's done and ready for you to move in. It sits on a nice, level yard on a

  Amanda Balaski Northwest CT Realty

  15 John St, Winsted, CT 06098
• 

  $321,000 Sold Aug 25, 2025

  • 2,623 Sq Ft
  • $122/SF
  • 7 Days On Market

  • 3 Beds
  • 5 Baths
  • Built 1900

  29 Walnut St, Winsted, CT 06098

  Introducing 29 Walnut: a grand Victorian home with a front porch view complimented by perennial rose gardens, a terrace fit for garden parties, and a large back yard. Upon entry, look upward to high ceilings, a spacious entryway and a grand, swirling staircase. Note precise finish work and period correct trim as you move into the open living, kitchen, and dining area with a chic half bath. Make

  Rosemary Scanlon Coldwell Banker Realty

  29 Walnut St, Winsted, CT 06098
• 

  Est $215,042 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  17 Front St, Winsted, CT 06098

  17 Front St, Winsted, CT 06098
• 

  

  /34

  $315,000

  • 2 Beds
  • 1 Bath
  • 1,880 Sq Ft

  101 Norfolk Rd, Winsted, CT 06098

  Beautifully updated Raised- Ranch retreat on 1.33 wooded acres! Nestled in a serene, natural setting yet conveniently close to local amenities. When you enter the home you will find two generous sized rooms with new vinyl plank flooring, fresh paint & a mini split as well as a spacious storage/utility room with laundry. The main floor includes the living room with a stone accent wall & great

  Jackie Desmarais Showcase Realty, Inc.

  101 Norfolk Rd, Winsted, CT 06098
• 

  $250,000 Sold Aug 22, 2025

  • 1,168 Sq Ft
  • $214/SF
  • 2 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1920

  233 Grantville Rd, Winsted, CT 06098

  Welcome to 233 Grantville Rd-a delightful 1,168 sq ft cottage-style home nestled on a quiet, level country lot in Winchester. Inside, you'll find a cozy kitchen, a comfortable living room, a modest bedroom, a small office, and a spacious bonus room that can serve as a second bedroom, family room, or flexible living space to suit your needs.The property also features an attached two-story

  David Sartirana Northwest CT Realty

  233 Grantville Rd, Winsted, CT 06098
• 

  Est $441,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  319 Taylor Brook Rd, Winsted, CT 06098

  319 Taylor Brook Rd, Winsted, CT 06098
• 

  

  /8

  $389,000

  • Land
  • 20.87 Acres
  • $18,639 per Acre

  7 Stadler Heights, Winsted, CT 06098

  Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39

  Hector Ortiz KW Legacy Partners

  7 Stadler Heights, Winsted, CT 06098
• 

  $425,000 Sold Aug 13, 2025

  • 2,086 Sq Ft
  • $204/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1970

  50 Lakeview Rd, Winsted, CT 06098

  Located just a short stroll from Holland Beach and only a 3-minute drive to the public boat launch, this charming Colonial offers the perfect blend of comfort, convenience, and year-round recreation. Nestled on a level corner lot in a well-established neighborhood, this home invites you to enjoy all the amenities of Connecticut's second-largest lake - from kayaking and boating to lakeside walks

  Paula Nelson William Raveis Real Estate

  50 Lakeview Rd, Winsted, CT 06098
• 

  Est $283,773 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  39 Rockwell St, Winsted, CT 06098

  39 Rockwell St, Winsted, CT 06098
• 

  

  /40

  $799,000

  • 5 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  151 Losaw Rd, Winsted, CT 06098

  Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-acre lot. This property is your personal sanctuary, complete with private trails for hiking your own land. The eat-in-kitchen is well-equipped with ample cooking space, seamlessly connected to the formal dining room and open to living space, and leads out to the large deck with

  Breanna Goebel Compass Connecticut, LLC

  151 Losaw Rd, Winsted, CT 06098
• 

  $320,000 Sold Aug 06, 2025

  • 1,752 Sq Ft
  • $183/SF
  • 24 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1963

  141 Maloney Ct, Winsted, CT 06098

  A charming ranch-style home, located in a desirable area, offers the convenience of single-level living. It features 4 bedrooms and 3 bathrooms, making it perfect for families or anyone in need of extra space. Upon entering the main floor, you'll find a spacious living room filled with natural light, which creates a warm and inviting atmosphere. The kitchen provides ample counter space and opens

  Marcy D'Angelo Coldwell Banker Realty

  141 Maloney Ct, Winsted, CT 06098
• 

  Est $206,154 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  111 Riverton Rd Unit 30, Winsted, CT 06098

  111 Riverton Rd Unit 30, Winsted, CT 06098
• 

  

  /13

  $199,900

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  14 Curtice St, Winsted, CT 06098

  Attention investors and buyers looking to build equity! Welcome to 14 Curtice Street, a home has incredible value and potential in the heart of Winsted. This 3-bedroom, 1-bath home features approximately 1,248 square feet of living space and is ideal for sweat-equity seekers or rehab-minded buyers. Exterior updates have already been completed, including a newer roof, siding, and windows, giving

  Michael Johnson Lock and Key Realty, Inc

  14 Curtice St, Winsted, CT 06098
• 

  $540,000 Sold Aug 06, 2025

  • 1,744 Sq Ft
  • $310/SF
  • 51 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  144 Marshall St, Winsted, CT 06098

  Welcome to your own private paradise! Nestled on an incredible 55 acres, this one-of-a-kind property offers peace, privacy, and the perfect blend of comfort and outdoor adventure. Featuring a ranch-style layout with 3 bedrooms and 2 full baths, this home is ideal for easy one-level living. Step inside to find hardwood floors throughout and three cozy fireplaces that bring warmth and character to

  Monica Palmerie RE/MAX RISE

  144 Marshall St, Winsted, CT 06098
• 

  Est $282,217 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  36 Charles St, Winsted, CT 06098

  36 Charles St, Winsted, CT 06098
• 

  

  /40

  $1,149,000

  • 3 Beds
  • 3 Baths
  • 2,097 Sq Ft

  674 E Wakefield Blvd, Winsted, CT 06098

  Experience premier waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath home offering stunning panoramic lake views and direct water access. Situated in the desirable 3rd Bay, this property boasts a private dock-perfect for boating, swimming, and enjoying all the lake lifestyle has to offer. Inside, you'll find an open and inviting layout with a spacious living

  Patrick Smith Smith & DeGroat Real Estate

  674 E Wakefield Blvd, Winsted, CT 06098
• 

  $800,000 Sold Aug 04, 2025

  • 1,488 Sq Ft
  • $538/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1928

  266 Perch Rock Trail, Winsted, CT 06098

  Wake up to sparkling water views and savor the serenity of lakefront living in this storybook Cape Cod-style retreat on Highland Lake's desirable east side. Tucked away on a peaceful private lane, this year-round haven offers 3 bedrooms & 2 full baths, perfectly blending classic charm with modern comfort. Step into the spacious kitchen, where sun-drenched mornings begin at the breakfast nook and

  Laurie Murray KW Legacy Partners

  266 Perch Rock Trail, Winsted, CT 06098
• 

  Est $433,905 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  43 Spencer St, Winsted, CT 06098

  43 Spencer St, Winsted, CT 06098
• 

  

  /27

  $235,000

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit H1, Winsted, CT 06098

  Discover effortless living in this inviting home at the sought-after Clockmaker's Hill community. The thoughtfully designed open floor plan creates seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining room, perfect for hosting friends and family. The sun-drenched kitchen features a convenient breakfast bar for casual dining and morning coffee. The

  Kim D'Andrea William Pitt Sotheby's Int'l

  174 Wallens St Unit H1, Winsted, CT 06098
• 

  $410,000 Sold Jul 31, 2025

  • 2,105 Sq Ft
  • $195/SF
  • 39 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1938

  17 Woodland Ave, Winsted, CT 06098

  Beautiful 3 bedroom updated colonial walking distance to Highland lake beach.Large eat in kitchen with granite counter tops,center island,bar area ,spacious sitting area with antique cooking stove that burns wood creates good heat.Living room with hardwood floors,fireplace and built ins.Nice patio off kitchen,yard is landscaped with fountains.2 car garage.This home is in great condition and wont

  Vincent DeVico Showcase Realty, Inc.

  17 Woodland Ave, Winsted, CT 06098
• 

  Est $213,127 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  111 Riverton Rd Unit 88, Winsted, CT 06098

  111 Riverton Rd Unit 88, Winsted, CT 06098
• 

  

  /34

  $625,000

  • 5 Beds
  • 3 Baths
  • 3,404 Sq Ft

  441 Platt Hill Rd, Winsted, CT 06098

  Welcome to 441 Platt Hill Road - a home that offers warmth, charm, and plenty of space to make memories. This inviting residence features an open and airy layout filled with natural light thanks to large windows and multiple skylights. Solid hardwood floors and tile run throughout the main level, creating a timeless foundation for your personal touch. The spacious eat-in kitchen, while vintage in

  David Sartirana Northwest CT Realty

  441 Platt Hill Rd, Winsted, CT 06098
• 

  $639,000 Sold Jul 31, 2025

  • 2,692 Sq Ft
  • $237/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  102 Hollow Hill Rd, Winsted, CT 06098

  Highest & Best Due by 6/17/2025 at 5PM. First time to the market this turnkey 2,692 sq ft Grand Ranch is nestled in on 2.78 bucolic acres surrounded by nature & mature trees. Lovingly maintained, this home provides the perfect set up for stress free living & entertaining boasting a large eat in kitchen with center island, dining area, SS appliances, dual wall ovens and propane cooktop, French

  Dawn Rousseau Showcase Realty, Inc.

  102 Hollow Hill Rd, Winsted, CT 06098
• 

  Est $368,477 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  155 West Rd, Winsted, CT 06098

  155 West Rd, Winsted, CT 06098
• 

  

  /20

  $249,900

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  22 Curtice St, Winsted, CT 06098

  Step into timeless elegance with this beautifully updated colonial-style home, where classic charm meets modern convenience. Gleaming hardwood floors flow seamlessly throughout the main living areas, creating a warm and inviting atmosphere. The fully renovated kitchen is a chef's dream, featuring premium finishes, sleek countertops, and top-of-the-line appliances. Upstairs, you'll find spacious

  Terence Dominick Complete Real Estate

  22 Curtice St, Winsted, CT 06098
• 

  $292,000 Sold Jul 25, 2025

  • 2,225 Sq Ft
  • $131/SF
  • 42 Days On Market

  • 6 Beds
  • 2 Baths
  • Built 1890

  126 Williams Ave, Winsted, CT 06098

  Excellent investment opportunity! This fully occupied two-family home generates a steady $3,300 in monthly rental income. The property has been completely overhauled in the past few years with almost everything updated. It is located in a great neighborhood in walking distance to all the schools in town. Close to playgrounds and the library. The recently painted exterior of this classic home

  Michelle Grant Coldwell Banker Premier Real Estate

  126 Williams Ave, Winsted, CT 06098
• 

  Est $393,408 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  133 E Wakefield Blvd, Winsted, CT 06098

  133 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /14

  $214,900

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft

  99 Norfolk Rd, Winsted, CT 06098

  99 Norfolk Rd, Winsted CT - Opportunity Knocks! This cute 3-bedroom Cape sits proudly on 1.3 acres and is ready for its next chapter! With vinyl siding, replacement windows, and a lovely setting perched high up from the road, the bones are here-now it just needs your vision. For those seeking an investment opportunity or ready to roll up their sleeves and bring this gem back to life, this could

  Lisa McCarthy Coldwell Banker Realty

  99 Norfolk Rd, Winsted, CT 06098
• 

  $1,200,000 Sold Jul 23, 2025

  • 2,407 Sq Ft
  • $499/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1948

  200 Perch Rock Trail, Winsted, CT 06098

  Exceptional Waterfront Living on Highland Lake - Your Dream Home Awaits! Seize this rare opportunity to own a stunning YEAR-ROUND WATERFRONT property on the highly sought-after EAST SIDE of Highland Lake! This turnkey gem is move-in ready and packed with modern features, offering the ultimate retreat for those seeking the serenity and excitement of lake life. Step into an open-concept kitchen and

  Annie Simard LPT Realty

  200 Perch Rock Trail, Winsted, CT 06098

Showing Results 41 - 80, Page 2 of 18